Dibromoacetic Acid → HCID 89613707, compound

HRID 623284

Reaction equation

HRID 623284 reaction equation
Cl.[Cl:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][N:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]2=[NH:16])=[CH:5][CH:4]=1.CCN=C=NCCCN(C)C.Cl.[Br:29][CH:30]([Br:34])[C:31](O)=[O:32]>CN(C1C=CN=CC=1)C.ClCCl>[Br:29][CH:30]([Br:34])[C:31]([N:16]=[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:10]1[CH2:9][C:6]1[CH:7]=[N:8][C:3]([Cl:2])=[CH:4][CH:5]=1)=[O:32]

Participants

6

Reactant 3

HCID 12433Dibromoacetic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86686930HCID 86686930, compound

Product 1

HCID 89613707HCID 89613707, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

200 mg (0.78 mmol) of the 1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-imine hydrochloride obtained by the method described in another method of Synthetic Example P1, 238 mg (1.95 mmol) of DMAP and 224 mg (1.17 mmol) of EDC-HCl were dissolved in 10 ml of anhydrous dichloromethane, 101 μl (202 mg, 1.17 mmol) of dibromoacetic acid was added thereto, and the resulting mixture was stirred at room temperature overnight. After the reaction was completed, the reaction solution was diluted with dichloromethane, washed once with water and twice with a 1% HCl aqueous solution, and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the subject material. Amount obtained 50 mg (yield 15%)

Workup

  1. washwashed once with water and twice with a 1% HCl aqueous solution
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto obtain the subject material
  5. customAmount obtained 50 mg (yield 15%)

Sources & evidence

ORD record
ord-ffdd7d0ce13447fcab851325e1354a4c
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Linked notes

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